cis-Nitromethylene neonicotinoids as new nicotinic family: synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-alpha]pyridine.
A series of neonicotinoids analogues of hexahydroimidazo[1,2-alpha]pyridine were modified at 5-, 6-, and 7-positions, and their insecticidal activities were evaluated. Introducing a methyl or ethyl at 7-position increased the insecticidal activities, while other substituents decreased activities. When alkyl substituents were introduced to 7-position, the insecticidal activities against Pea aphids decreased in the order methyl (7a)>ethyl (7b)>n-butyl (7e)>phenyl (7f)>n-propyl (7c)>iso-propyl (7d), p-NO(2)-phenyl (7g). Modifications at 5-, 6- or both at 6- and 7-positions with methyl or ethyl were unfavorable to activities. Interestingly, introducing methyl to 7-position not only increased insecticidal activities against pea aphids, but also show higher insecticidal activities than imidacloprid against imidacloprid-resistant brown planthopper.
Shao
Xusheng
X
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Zhang
Wenwen
W
Peng
Yanqing
Y
Li
Zhong
Z
Tian
Zhongzhen
Z
Qian
Xuhong
X
D000818:Animals; D002626:Chemistry, Pharmaceutical / Q000379:methods; D018360:Crystallography, X-Ray; D015195:Drug Design; D007093:Imidazoles / Q000138:chemical synthesis / Q000494:pharmacology; D007313:Insecta; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology; D008956:Models, Chemical; D008968:Molecular Conformation; D000073943:Neonicotinoids; D009539:Nicotinic Acids / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D011978:Receptors, Nicotinic / Q000737:chemistry*; D012306:Risk
D007093:Imidazoles; D007306:Insecticides; D000073943:Neonicotinoids; D009539:Nicotinic Acids; D009574:Nitro Compounds; D011725:Pyridines; D011978:Receptors, Nicotinic; C082359:imidacloprid